1-Butanol → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

HRID 2247094Notes

Reaction equation

HRID 2247094 reaction equation
[CH3:1][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[C@H:15]([OH:24])[CH2:16][C@H:17]([OH:23])[CH2:18][C:19]([O:21]C)=[O:20])=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].[OH-].[Na+:33].C(O)CCC>CC(C)=O>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:24])[CH2:16][CH:17]([OH:23])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:33]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 14798Sodium HydroxideHCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 53.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Fluvastatin methyl ester (2.0 g) was added to a mixture of NaOH (1 eq.) and butan-1-ol (15 ml). The mixture was stirred at about 80EC for 1.5 h, after which the starting material was not detected by HPLC. Then, 40 ml of acetone was dripped into the solution and the mixture was cooled slowly to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetone (20 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 1.09 g (53.5%) of fluvastatin sodium Form VII.

Workup

  1. stirringstirred overnight
  2. customThe product was isolated by filtration under nitrogen
  3. washwashed with acetone (20 ml)
  4. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-8173d3028ca24bc4bd39fa932212aae9
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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